Vacation rentals with a fireplace in Berkshire County

4.86 out of 5 average rating, 290 reviews

A rustic cabin is nestled in a wooded area, featuring a bright red front door and a spacious deck. Surrounding the deck, lush greenery provides a natural backdrop, and a cozy seating area is visible on the porch. A fire pit with stones is situated in the foreground.

Cabin in Stephentown

Cabin in the woods w cedar Hot Tub + private pond

The Hemlock Hideaway is a charming, rustic cabin in the woods designed for rest and relaxation. Guests will journey into simpler times, inspired by antique furnishings that remind them to slow down and unwind during their stay. The cabin is isolated yet only 10 min drive to Jiminy Peak for skiing as well as park and trails for hiking, apple orchards, excellent restaurants and foliage viewings. Cherry Plain State Park, Mount Greylock, Lebanon Speedway, Albany, and Pittsfield are all 25 min max.

4.99 out of 5 average rating, 332 reviews

A brown hen is seen foraging among the green foliage and fallen leaves. The bird's feathers are a warm shade of brown, blending with the earthy tones of the surroundings. Branches and leaves create a natural frame around the hen.

Loft in Great Barrington

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

4.94 out of 5 average rating, 417 reviews

An expansive deck is surrounded by lush greenery, featuring outdoor seating and a dining area. Warm café lights hang overhead, creating a cozy atmosphere. A person is seen grilling at a gas grill, while another enjoys a meal at a table, capturing a serene outdoor experience.

Chalet in Otis

Mid-Century Glass Octagon in the Berkshires

This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

4.94 out of 5 average rating, 212 reviews

A private dock extends into the calm lake, featuring a sliding board and a set of stairs leading into the water. A rustic playhouse sits nearby, complemented by a wooden bench. Colorful Adirondack chairs surround the area, offering serene views of the surrounding nature.

Cottage in Becket

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • 50" smart TV and 4 Google Smart Speakers • 1 Gigabit Wi-Fi 'gorgeous with amazing views' • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Apartment in Copake Falls

A bright and airy living space features a round wooden dining table surrounded by black chairs. Large windows invite natural light, offering views of the scenic outdoor landscape. A seating area with a black sofa is positioned beside a modern fireplace, enhancing the room's comfort.

4.91 out of 5 average rating, 331 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

4.99 out of 5 average rating, 297 reviews

A whimsical structure features a unique tree integrated into its design, with wooden shingles and a peaked roof. Sturdy stairs lead to the entrance, surrounded by lush greenery. Large windows provide glimpses of the enchanting architecture, enhancing the magical ambiance of the setting.

Treehouse in Tyringham

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

4.97 out of 5 average rating, 214 reviews

A cozy outdoor space features a wooden pergola with string lights, providing a warm ambiance. Comfortable seating is arranged around a table on a stone patio, with a barbecue grill positioned nearby. Lush green grass surrounds the area, accentuating the peaceful environment.

Home in Lee

Berkshire 4 season home

The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Cottage in Great Barrington

A charming cottage exterior is framed by lush greenery and vibrant flowers. The inviting red door is adorned with a decorative wreath, while large windows display rustic charm. A wooden fence adds an element of privacy, complementing the tranquil setting of this quaint getaway.

4.94 out of 5 average rating, 294 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

4.9 out of 5 average rating, 107 reviews

A serene outdoor setting is displayed with two black Adirondack chairs positioned on a wooden deck. Surrounding greenery includes leafy trees, and a gentle stream flows nearby, enhancing the natural ambiance of the space.

Cottage in Becket

Stylish Shales Brook Cottage-Cozy up to happiness

Bright & inviting! Welcome to our charming cottage, a stylish 2-bedroom, 2-bath retreat by Shales Brook. Relax on cool evenings beside the vintage Malm wood-burning stove. Enjoy modern comforts with central air, a screened-in porch, and a deck overlooking the tranquil waters of Shales Brook. The soothing sounds of the brook enhance your stay.. Located near fabulous Berkshire attractions, fantastic hikes, 15 minutes to the town of Lee, minutes to Jacob‘s pillow and 20 minutes to Tanglewood,!

4.97 out of 5 average rating, 262 reviews

A spacious living area is highlighted by tall windows, allowing natural light to fill the room. A stone fireplace is central to the seating arrangement, which includes a light-colored sectional sofa and accent chairs. Neutral tones and wood accents create a warm ambiance.

Home in Great Barrington

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

4.9 out of 5 average rating, 126 reviews

A flowing stream is nestled among lush greenery, bordered by tall trees and dense foliage. Clear water glistens as it travels over smooth stones, with soft ripples audible in the serene environment.

Yurt in Stephentown

Off Grid Yurt Right By The Best of The Berkshires

This is an off grid yurt with a woodstove for heat and an off grid kitchen - no running water or electricity - water can be heated on the woodstove. You'll have a comfy bed and futon. We love it when it rains. Staying inside, listening to the rain on the yurt and playing games is a highlight of our trips there. Cooking outside and enjoying a campfire & toasting marshmallows is also fun!

4.97 out of 5 average rating, 560 reviews

A circular structure is set in a wooded area, partially surrounded by snow-covered ground. Warm light spills from the open doorway, contrasting with the cool tones of twilight. Trees with bare branches frame the scene, creating a serene winter ambiance.

Apartment in North Adams

Steps to MoCA: 2bd + SAUNA!

A large and private 2 bedroom apt at the Small Mansion of Chase Hill, 3 mins by walk to Mass MoCA. 10 mins drive to Williams College, Clark. 5 mins walk to downtown’s restaurants. Whimsically restored (yes, fast Wi-Fi & great water pressure). Part of @chasehillartistretreat YOUR STAY HERE ENABLES US TO HOST REFUGEE/IMMIGRANT ARTISTS PRO BONO!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Berkshire County fireplace rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a fireplace

4.96 out of 5 average rating, 54 reviews

A hot tub is positioned outdoors on a wooden deck, surrounded by tall trees. Fresh towels are neatly arranged on a small table nearby. The serene lake, framed by lush greenery, is visible in the background, indicating a peaceful outdoor retreat.

Home in Canaan

Private Retreat: Hot Tub! Movie Room! Pool Table!

MusserRating, 5 stars1 week ago

This was a bit of a last minute decision to come to the Berkshires and I was grateful that Tiffany could accommodate some quick changes. The house is just as described--lots of space, nice setting, pool table was fun (and cool in the basement), and I appreciated that our two dogs could be included. Even though the house is in NY, it is not far from the hiking trails and museums. We would like to come back--a lot more to see and do in this area.

4.99 out of 5 average rating, 156 reviews

A historic white house is surrounded by lush green grass and trees. The two-story structure features a covered porch on one side, with large windows reflecting the natural light. Scenic hills are visible in the background, adding to the serene countryside setting.

Home in Dalton

Cleveland House - renovated Berkshires' gem.

InessaRating, 5 stars3 days ago

We had a lovely stay at Elizabeth's place. The house was big enough for our large group, the kitchen was well stocked with anything we might need, and the area was peaceful and beautiful.

5 out of 5 average rating, 66 reviews

Home in Canaan

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove

MichelleRating, 5 stars1 week ago

We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

4.89 out of 5 average rating, 146 reviews

A spacious living area is furnished with a light-colored sectional sofa, a cozy armchair, and a coffee table, all arranged around a stone fireplace. Natural light filters through the large windows, enhancing the warm wooden flooring and highlighted by subtle wooden beams.

Home in Hillsdale

Fenced yard, playroom & the Berkshires - $0 fees

SophiaRating, 5 stars2 weeks ago

The house was clean and nice! Beds were huge and comfortable and the area is beautiful. The hosts were very responsive. It was the perfect trip.

5 out of 5 average rating, 12 reviews

A spacious living area features high, vaulted ceilings and large windows that frame views of the outdoors. Two comfortable sofas are arranged around a central area rug, with a stone fireplace serving as a focal point. Shelving units display various decorative items, while a light floor lamp adds illumination.

Home in Great Barrington

Valley Vista atop Jug End

PanosRating, 5 stars1 week ago

Nice place. Great layout. Easy to navigate. Host was very communicative. We would stay there again.

4.95 out of 5 average rating, 174 reviews

A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.

Home in Pittsfield

Cantabile life in the Berkshires

BillRating, 5 stars1 week ago

Jia place was great. Very spacious and plenty of things to do. It was very clean. The entire process was super simple. We enjoyed it quite a bit.

4.95 out of 5 average rating, 132 reviews

An entryway features a grey console table with glass-front cabinets, topped by a table lamp and a potted plant. A round mirror hangs above the table, while a doorway leads into the home, revealing glimpses of the kitchen and hallway beyond.

Home in Stockbridge

Sun-filled, Charming Stockbridge Classic- In Town!

MichaelRating, 5 stars1 week ago

Great location and house. Will definitely recommend to others who wish to stay in the Berkshires! Thanks so much for your flexibility!

4.9 out of 5 average rating, 125 reviews

The exterior of the house is showcased, featuring a red wood siding that complements the natural surroundings. Lush green grass and trees frame the property, while a hint of blooming foliage adds subtle color. The structure includes multiple sections with a sloped roof and chimney.

Home in Egremont

Beautiful Period Home in the Berkshires

AmberRating, 5 stars3 weeks ago

We really enjoyed the our girls weekend in the Berkshires! The house had plenty of places to sit and hang out, which was especially useful because it was a rainy weekend. The house is in very private and in the woods, and was great for bird watching. It is also very close to Great Barrington with lots of restaurants. We would definitely stay again!!

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Apartment rentals with a fireplace

4.86 out of 5 average rating, 29 reviews

An outdoor pool area is surrounded by several lounge chairs and umbrellas, offering a view of vibrant autumn foliage on the hills. The pool is partially covered, and a building is visible in the background, enhancing the resort-like atmosphere.

Apartment in Hancock

Mountainside Condo Ski on/off

ThomasRating, 5 stars3 months ago

A great place for a skiing getaway at Jiminy Peek Resort! Ski - in, ski -out, a lovely appointed condo, with access to a hot tub. Frank was most helpful and friendly. I highly recommend his place.

Apartment in Great Barrington

A dining area is seen with a round wooden table surrounded by six wooden chairs. A large window allows natural light to fill the room, while a lamp stands on the table. The walls are painted a soft blue, complemented by a red carpet underfoot.

4.78 out of 5 average rating, 18 reviews

Writer's retreat: study, books, fireplace (Ecobnb)

MelaRating, 5 stars7 months ago

The location and space were great! I worked remotely during most of my stay and was very comfortable with my set up. The dining table was a perfect desk, with good lighting and wifi! Slept well due to it being so quiet at night. A positive experience overall.

Apartment in Great Barrington

A bright sunroom features large windows that allow natural light to illuminate the space. A gray and white patterned rug lies on the floor, complementing a cozy seating area with yellow cushions. A green dining table with chairs and potted plants add a touch of color.

4.89 out of 5 average rating, 28 reviews

Zen River Studio

katherineRating, 5 stars3 weeks ago

We loved the studio and felt right at home It was a perfect place to stay while exploring the Berkshires, close to both outdoor activities and the offerings of the town. We especially appreciated the beautiful view from the studio which enhanced rest and relaxation. Jill and Steve were great hosts. Highly recommend.

5 out of 5 average rating, 11 reviews

A cozy living area features a tall Christmas tree adorned with lights and ornaments next to a glass-top coffee table. A fireplace with built-in decor sits beneath a mounted television. Velvety blue chairs complement an orange accent pillow on the nearby couch, surrounded by large windows with sheer curtains.

Apartment in Hancock

Artsy loft near MassMoCA with pool and hot tubs

GinaRating, 5 stars3 days ago

The absolute perfect location at the heart of the Berkshire Yoga Festival! Loved the location. Very comfortable for two people. The host was very quick to respond and was accommodating. I would definitely recommend and would stay there again.

Apartment in Lanesborough

A wooden sign with a circular cutout features the name 'Second Drop Farm' prominently displayed in metallic letters. Inside the circle, a metal silhouette of a tree is depicted, showcasing intricate branches and roots against a rustic wooden background.

4.89 out of 5 average rating, 127 reviews

Cozy Rustic Apt. in 18th c. Berkshire Farmhouse

IsaihaRating, 5 stars1 month ago

Wonderful place to stay for an anniversary clean rustic apartment with a welcoming feeling, it felt like a cabin 10/10 would recommend 🙂‍↕️

4.91 out of 5 average rating, 456 reviews

The living area features warm wooden floors and a cozy seating arrangement, including a sofa and an armchair. Light pours through the window, illuminating a colorful area rug and a coffee table adorned with books. A pair of opened doors leads to the spacious bedroom, showcasing a bed with decorative bedding.

Apartment in North Adams

Private guest apartment. One block from downtown.

KelseyRating, 5 stars3 weeks ago

Jennifer’s place was lovely - extra touches like snacks and fresh flowers were very much appreciated! Great location easy to walk to town!

Apartment in Great Barrington

An outdoor patio area features a stone surface surrounded by colorful flower beds. A round table with chairs and a large umbrella provide seating, alongside a charcoal grill. The home's entrance is highlighted by a welcoming red door and large windows.

4.92 out of 5 average rating, 194 reviews

Secluded but not isolated Berkshire Retreat

GretchenRating, 5 stars5 months ago

This was our 2nd weeklong stay. The space is clean and bright. Heating details were clearly explained. It was quiet and peaceful but only a 7 minute drive for milk I forgot to bring for coffee. We saw a small bobcat in the front yard on our last morning. Beds were very comfortable. Hosts were friendly and responsive. I’d recommend this place to friends/family and hope to stay again.